Bessie Head was one of the Drum writers of the 1950s. As critics such as Huma Ibrahim have indicated it was only after her death in 1986 that she was included in discussions on the Drum generation. The result of her prior exclusion has been the double marginalization of Head's literary contribution, as one of the overlooked black South African writers of the 1950s and the lack of critical acclaim of her as an individual author. For this reason, she is one of the black South African writers who should consciously be given prominence today. This article utilizes an analysis of Head's novels not attempted so far. It is difficult to interrogate Head's work fruitfully, unless questions are addressed to whether she approaches her imaginative writing as an Africanist, a feminist or just as a woman. It will be argued that her fiction highlights the plight of the socially marginalized in eccentric and seminal ways and that it bears the potential to enrich debates on Africanism, feminism and womanism. Conclusions on how the complexities of Head's psyche can be beneficially used to enrich a more judicious reading will be drawn from evidence gathered from her novels.